Ethyl Acetate → methyl 3-methyl-2-oxo-2,3-dihydro-1H-benzo[d]imidazole-5-carboxylate

HRID 1892602Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1892602
[C:1](C1NC=CN=1)(C1NC=CN=1)=[O:2].[NH2:13][C:14]1[CH:23]=[CH:22][C:17]([C:18]([O:20][CH3:21])=[O:19])=[CH:16][C:15]=1[NH:24][CH3:25].C(OCC)(=O)C>O1CCCC1>[CH3:25][N:24]1[C:15]2[CH:16]=[C:17]([C:18]([O:20][CH3:21])=[O:19])[CH:22]=[CH:23][C:14]=2[NH:13][C:1]1=[O:2]

Komponenten

5

Edukt 3

HCID 8857Ethyl AcetateHCID 5250894Bis-(1H-imidazol-2-YL)-methanone2×HCID 57835341Methyl 4-amino-3-(methylamino)benzoate

Produkt 1

HCID 67151300methyl 3-methyl-2-oxo-2,3-dihydro-1H-benzo[d]imidazole-5-carboxylateAusbeute 64,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Add carbonyl diimidazole (587 mg, 3.50 mmol) to a solution of methyl 4-amino-3-(methylamino)benzoate (586 mg, 3.19 mmol) in tetrahydrofuran (20 mL) at room temperature. Stir the yellow solution at room temperature for 16 hours. Add carbonyl diimidazole (500 mg, 0.96). Stir at room temperature for 4 hours. Add ethyl acetate (75 mL). Wash with 10% citric acid (5 mL), 1N sodium hydroxide (5 mL), and brine (5 mL). Dry the organics over magnesium sulfate, filter, concentrate, and dry under high vacuum to yield a crude yellow solid (690 mg, 100%). Triturate this crude solid with ethyl acetate (10 mL). Filter the precipitate and dry under high vacuum to yield methyl 3-methyl-2-oxo-2,3-dihydro-1H-benzo[d]imidazole-5-carboxylate (422 mg, 64%). 1H NMR (400 MHz, CDCl3) δ ppm 3.46 (s, 3H), 3.92 (s, 3H), 7.12 (d, J=8.21 Hz, 1H), 7.68 (s, 1H), 7.84 (dd, J=8.31, 1.47 Hz, 1H), 9.87-10.03 (m, 1H).

Aufarbeitung

  1. stirringStir at room temperature for 4 hours
  2. washWash with 10% citric acid (5 mL), 1N sodium hydroxide (5 mL), and brine (5 mL)
  3. dry with materialDry the organics over magnesium sulfate
  4. filtrationfilter
  5. concentrationconcentrate
  6. customdry under high vacuum
  7. customto yield a crude yellow solid (690 mg, 100%)
  8. customTriturate this crude solid with ethyl acetate (10 mL)
  9. filtrationFilter the precipitate
  10. customdry under high vacuum

Quellen und Nachweise

ORD-Eintrag
ord-a5f0cf5f54f84761906ae83ac1b473d4
Quelldatensatz
uspto-grants-2013_08
Patentnummer
US08507681B2

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